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Siesta Key Villas

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    Travellers to Siesta Key are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    34 Matching Rentals in Siesta KeyView all 531 rentals
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    Jamaica Royale #100-Peaceful Gulf Side Condo1 / 44
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Luxury Villa, Sleeps 6 Comfortably Located on Siesta Key Beach, Sarasota Florida1 / 26
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Siesta Villa Palma1 / 66
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the beauty of Siesta Key at Siesta Villa Whispering Palms. Our recently renovated 3-bedroom, the 2-bathroom stand-alone villa is your new home-away-from-home. Featuring 1700 sqft of air-conditioned living space, an open floor plan, large living spaces, spacious bedrooms, and well-manicured...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the global flair of Siesta Key, Villa Soleil! This beautiful, stand-alone villa has 3 bedrooms, 2 baths and boasts fine appointments throughout. It’s an eclectic and artistic mix of French and Asian décor met by coastal pops of color and high-quality design. It’s extravagant and comfortable....
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    About this property
    Welcome to La Estrella Casita! This gorgeous freshly remodeled beach casita is the perfect getaway for you and your closest friends and family! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    If you're dreaming of a scenic seascape getaway, this recently remodeled Bianco Sands’ is the perfect vacation home for you. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. Situated...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Spacious 4bed air-con villa on Siesta Key1 / 26
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2016
    This lovely 4-bed villa was well proportioned and kitted out for our party of 6 adults but deciding who should get the biggest and best bedroom with the only en-suite could have...
    Reviewed July 21, 2015
    We stayed two weeks here and had a wonderful time. The villa was very spacious with large bedrooms, eat-in kitchen and living rooms. Most impressive was how well equipped it...
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    About this property
    Very spacious, air-conditioned 4 bed detached ranch-type Villa on Siesta Key Bayside. Sleeps 8, 1 King, 1 Queen, 2 Full and 2 twin beds. 1 month minimum Jan-March, 2 week minimum April -Dec. Maximum 3 cars . Large Heated Communal pool, Own Outdoor patio area with BBQ , Table, seating and sun...
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    Siesta Key, Florida FL34242
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
    Sunset Point Siesta Key FL  AWESOME RENTAL !!1 / 27
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Patio
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    • Sauna
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2017
    Could not have a better location. Steps from the sand with the village in walking distance. The beach house is a great place to stay. Everything you need. We very much enjoyed...
    Reviewed July 7, 2017
    This location is absolutely perfect! It is on the most beautiful beach and steps to an adorable village with several restaurants, shops and all the amenities you could need. It...
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    About this property
    Beach and water front on Gulf Of Mexico. A block from Siesta Key Village for lite and fine dinning, fun, shopping and nightlife. Two Master Suite King Bedrooms with Master Bath for each. Sauna, four Mexican tiled decks with panoramic views of the Gulf and beaches. Fishing Pier. Leather, stone...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Villa Laughing Gull - Cozy, Private Siesta Key Villa1 / 29
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2017
    We just got back from our stay at the Siesta Villa Laughing Gull. It is a wonderful 2 bedroom home. Everything is as pictured and stated in description. We stayed with a family...
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    About this property
    The Property Find yourself in the relaxing comforts of Siesta Villa Laughing Gull. A single-story stand-alone villa, located in the beautiful private community of Polynesian Gardens, on the tropical barrier island of Siesta Key, Fl. The peaceful tranquility of Siesta Villa Laughing Gull is the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Home Enjoy the luxury and amenities of Siesta Key from the comfort of your own private villa. Exquisitely decorated, encompassing the ambiance and excitement of Siesta Key, the Great Blue Heron provides you with all the luxuries and comforts you will need for the perfect beach getaway....
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Property Siesta Villa Coralline is a stand-alone single story villa located in the beautiful community of Polynesian Gardens on Siesta Key. Villa Coralline has been designed & decorated as an upscale beach cottage featuring two bedrooms, one with a King bed and the second with two twins. The...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Central Heating
    • Terrace
    • DVD Player
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Home Welcome to the adorable coastal stylings of Casa Covella. Located within the private community of Polynesian Gardens, Casa Covella is a private stand-alone villa on the Inter-coastal Waterway side of Siesta Key island. Recently remodeled in the summer of 2018, Casa Covella is a...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Siesta Key private beach access1 / 51
    (35)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Patio
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    • Balcony
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2018
    This place was very well kept, clean and plenty of supplies for the beach and pool as well as fully stocked kitchen for cooking and serving. The accommodations were perfect for...
    Reviewed January 10, 2018
    This well appointed, spacious townhouse is a short walk to the spectacular Crescent Beach. The townhouse is well appointed with EVERYTHING you could possibly need. It had...
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    About this property
    Beachside, spacious 3 bedroom, 2500 square foot, beach townhouse located among the resort community of Sara Sea Circle with direct, private beach access to the world famous (rated #1 in USA) Crescent and Siesta Key Beaches. The Sara Sea Circle community includes a large heated pool, sand...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    NEW EVERYTHING  Luxury King  villa #1 Siesta Key  Heated Pool  Walk to beach1 / 7
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    Villa 1 is an end villa You can park outside in front Feels private Nice and bright Everything is new after a full property remodel 2017 An open living room withe the kitchen and dinning area 55 inch HDTV Full size stainless steel fridge Microwave,Coffee maker and toaster 2 burner cook top Granite...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Newly remodeled with beach and Pool Access!! -Crescent St. Perlita.1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Reviewed March 11, 2019
    Very clean and nicely remodeled unit. Beds were comfortable and just steps away from the heated pool out back. Any issues or concerns were quickly addressed by management (had a...
    Reviewed February 17, 2019
    Clean freshly remodeled home that is a 4 minute walk to the beach. Also includes a pool that has different colored lights at night. Beachside management was easy to deal with...
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    About this property
    Welcome to La Perlita Casita! This gorgeous freshly remodeled beach casita is the perfect getaway for you and your closest friends and family! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful location on Siesta Key1 / 12
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Villa is located on the bay side of Siesta Key with walking distance (deeded access) to white sanded beaches (4 minutes). Has partial water view and full pool view. Close to the Siesta Key village, famous restaurant, shops, rental facilities with boats, yet ski, bike and more. Villa consists of...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Retreat to this amazing “Sea”-cluded gem tucked into the lovely Bianco Sands complex- just a short stroll to the warm sands of Crescent Beach and the lively Crescent Village. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Only 150 yards to Crescent Beach and heated pool!1 / 58
    (23)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 6, 2019
    Host's were great with communication, and the place was adorable and affordable. Nice pool access and easy walk to the beach.
    Reviewed June 22, 2019
    This place was just right for my wife and I and two boys age 6 & 9. Most of the time spent on the beach and kayaking with the kids. Perfect place to stay. Very short walk to...
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    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Siesta Key Oceanfront on Gulf with western sunsets,  1250 sq ft Townhome1 / 15
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Grill
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    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gorgeous updated townhouse located right on the Gulf of Mexico’s Big Sarasota Pass with spectacular western views that can be filled with amazing sunsets, fishing boats, dolphins, and more. Great location for fishing or viewing off the community’s private dock. Waterfront views from master bedroom...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    This gorgeously remodeled beach casita is the perfect getaway! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. The décor is beautifully done and inspired by the soft tones of the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Only 150 yrds to Siesta Key Beach and heated pool!1 / 50
    (22)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Washer
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    • Cable/satellite TV
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2019
    Clean place. Walking distance to the beautiful beach. across from restaurants and shopping stores. Owner responded fast to inquiries. Will definitely Nena l again.
    Reviewed May 29, 2019
    You can not ask for a better location. So close to the beach and pool. Yes, it's on a busy street but that also means no walk to catch a trolley. Also great restaurants and gift...
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    About this property
    Newly upgraded ( September 2015 ) with new kitchen, new vanities, newly painted and with the tiles steam cleaned this Siesta Key villa is a gem. It comes with a with a lovely heated community salt water pool and private access to the beautiful white sanded Crescent Beach! Crescent Beach on Siesta...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Central Heating
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    Smoking allowed
    About this property
    1000 square feet This gorgeously remodeled beach casita is the perfect getaway! Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. The décor is beautifully done and inspired by the soft...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This spacious one-bedroom suite offers a full beach view from the living room and located 200’ from the quartz powder white sand. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. This...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Stunning remodel with all new furnishings, One queen bed, and two twins in the second bedroom, Queen sofa bed in living room, one bathroom. Siesta Key duplex with private and gated Beach Access just steps away to the beautiful crystal sands and community pool, located in the heart of the vibrant...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This spacious one-bedroom suite offers a courtyard view and located 200’ from the quartz powder white sand. Included with your stay: Complimentary Bicycles, Beach chairs, Beach-Towels, Free-rides around Siesta and a 7-day week office for your convenience and guest needs. This room has a renovated...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Deluxe 3-BR Siesta Key Townhouse - Heated Pool - Siesta Key Village1 / 34
    (40)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 2019
    We have gone back 7 of the last 9 years. Amazing location. Very comfortable. It is really close to beach entrance #5 which is the best part of the beach. 1 minute walk to the...
    Reviewed March 8, 2019
    We have been renting in Seaside Villas for ten years, both in the one bedroom and the three bedroom units. The location is fantastic, the owner and property manager are great...
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    About this property
    SEASIDE VILLAS - Deluxe 3-Bedroom Siesta Key Townhouse Vacation Rental - With Heated Pool   Located in the Heart of Siesta Key Village, Sarasota, FL - Short Walk to Crescent Beach   SEASIDE VILLAS: This Siesta Key deluxe 3-Bedroom townhouse rental is located in the heart of Siesta Village – just...
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    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Escape the cold in beautiful Siesta Key, Florida. 2 bedroom 2 bath villa at Provincial Gardens. Spend your winter sitting on the beach or swimming in the Olympic size pool at Aloha Kai. Enjoy the tropical landscape in your private courtyard or spend the evening on the pier watching fish and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Our beautiful Villa is located right on America's #1 Beach (Siesta Key) in Sarasota, Florida. Take about 200 steps and you're on the notorious white sand beach itself. It is located within walking distance of shops and restaurants, and also has many water sport rental options close by! Come and...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casual Elegance can best describe this charming 1 Bedroom 1 Bath Villa on world famous Siesta Key Beach. This unit was re-modeled during the summer of 2014 by new owners and offers a crisp clean look and vibe for your vacation escape. The unit received numerous upgrades. Everything in the unit is...
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    Siesta Key, Florida 34242
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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    About this property
    Beautiful remodel with all new furnishings, 2 Bedroom/ One Bath: One queen bed, and two twins in the second bedroom, Queen sofa bed in living room, one bathroom. Siesta Key duplex with private and gated Beach Access just steps away to the beautiful crystal sands and community pool, located in the...
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    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    CASA BLANCA B17 2 Bdrm, 2 bath Villa on Crescent Beach1 / 15
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 18, 2018
    A fantastic place for a family. 5 night stay with my wife and 2 boys. Easy check in, place was clean and updated and everything was provided. Family loved the beach and pool...
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    About this property
    Modern Clean, Well Appointed Stand Alone Villa, 2 bdrm-2bath. PrivateUltra Hi-speed internet 150 mps, 3 tv's , Whole house DVR, Sleeps 4. Fully equipped kitchen, computer desk in living room, dual recliner leather sofa, Lazyboy reckliner, HD TV with DVR 280 channels and free Starz movies, fee free...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Deluxe 4-BR Siesta Key Townhouse & Garden Apt - Heated Pool - Siesta Key Village1 / 38
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    Check in Check out
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    Amenities & Details
    • Internet Access
    • Grill
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 18, 2016
    My two children, their spouses and three grandchildren (12, 9 and 6) and I spent an idyllic week on Siesta Key a few weeks ago. Instead of renting a high-rise condo, we opted...
    Reviewed July 26, 2015
    We came back this year to stay with family and had just as good of a time. The place is immaculate and the location can't be beat. They were very attentive to any needs and if...
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    About this property
    SEASIDE VILLAS - Deluxe 4-Bedroom Siesta Key Townhouse Vacation Rental - With Heated Pool   Located in the Heart of Siesta Key Village, Sarasota, FL - Short Walk to Crescent Beach   SEASIDE VILLAS: This Siesta Key deluxe 4-Bedroom townhouse (3BR plus 1BR garden apartment) rental is located in the...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
    Beachwalk - Siesta Key Beach - 3BR Townhouse - Heated Pool - upscale1 / 35
    (35)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Show Prices
    Amenities & Details
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2019
    This was a fabulous location, one block from the beach. This place was fully capable of hosting a large family. It has everything you could need; plenty of towels, stocked...
    Reviewed June 22, 2019
    This unit was spacious and clean, right across from one of the most beautiful beaches in the country! The amenities were very good, except you do really need to have working...
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    About this property
    BeachWalk Siesta Key Townhouses Across from Crescent Beach Three Bedrooms - Heated Pool - Private Elevator   Located across from Siesta Beach and five blocks from Siesta Key Village, Sarasota, FL   BEACHWALK Townhomes; Three bedrooms, two and a half baths, garage, heated pool (shared with...
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    Location Information
    Siesta Key, Florida 34242
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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